


Peeping Jack

by LightLeadingMe



Category: Will & Grace
Genre: F/M, Masturbation, Smut
Language: English
Status: Completed
Published: 2018-08-05
Updated: 2018-08-05
Packaged: 2019-06-22 00:51:08
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 1,332
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15570108
Author URL: https://archiveofourown.org/users/LightLeadingMe/pseuds/LightLeadingMe
Summary: Jack accidentally walks in on Karen and Malcolm and can't get the image out of his head.





	Peeping Jack

Jack stared in the open doorway of Karen's library, his jaw practically on the floor. There, on the ladder against the bookshelves sat Karen, her head tossed back and thumping against one of the rungs as Malcolm thrust into her. The business man was partially dressed, his shirt loosely open and his pants hanging around his hips. Karen still had her dress from earlier that morning on, but it was bunched up around her waist and the bodice was tugged down, her bare breasts bouncing with each thrust of Malcolm's hips. Jack recalls commenting on how amazing her tits looked in the dress just a few hours ago, but he realized that nothing compared to the way they looked now. He swallowed loudly, willing his feet to take him away from where he was, but he couldn't move, his body frozen and his eyes glued to the sight of Karen getting fucked by her boyfriend.

It should have been repulsive, an unsightly thing for a gay man to witness, but he found that he was almost unwilling to look away. He observed his best friend in the throws of passion, one hand holding the back of Malcolm's neck and her arm above her head, hand clutching the ladder so tightly he could see the whites of her knuckles. A leg was hooked around Malcolm's hip, her high heel digging into the back of his thigh and the other was spread out to the side, foot propped on a table to keep her balance. Her mouth was open as she gasped and her eyes were closed, sweat beginning to form on her forehead and chest. Malcolm was making low groaning sounds, whispering "baby" to her every few seconds to which Karen would whimper sexily. His eyes traveled lower and he gulped.

Karen was right; Malcolm had enormous genitalia.

When he brought his eyes back to her face, she was staring right at him and he felt like his body was about to shut down. His cheeks were red with embarrassment, yet he still couldn't move, terrified of the fact that he had been caught staring. He waited for Karen to start screaming, tossing obscenities his way, demand Malcolm stop so he could throw him out, but nothing of the sort happened. Jack felt like he body caught fire when Karen just grinned slowly, her eyes hooded in passion as she continued to watch him watching her. And then she came, a drawn out moan vibrating past her lips. He heard a grunt emit from Malcolm followed by an obnoxious cry of "Oh baby!" and Jack assumed that Malcolm came as well. But his eyes never left Karen's, even as she pulled Malcolm down to her lips for a kiss, Karen held his gaze. The kiss only lasted a few seconds and he heard Malcolm mutter something, causing Karen to look at him and then suddenly Jack could move again, gaining back control over his legs. He tore out of the manse like the building was on fire and didn't stop running until he was safely behind his door of 9A. 

Hours had passed and it was now nearing midnight, but Jack couldn't sleep. He tossed and turned in his bed, the mental image of Karen in the throws of passion seared into his mind and preventing him from slumber. If he was honest, it was one of the hottest sights he had seen, which confused him like never before. He squeezed his eyes shut and saw her staring at him, heard her moan as she came, saw his own cock thrust in and out of her wanting body. Jack's eyes popped open and he sat up, the sheets falling to his waist as he breathed heavily. He stared down into his lap where the bedding gathered and realized he was fully erect, the satin sheets forming a perfect tent. He licked his lips and swallowed audibly before laying back down, resting his head on the pillow as his legs kicked the sheets off. He smoothed a hand down his own chest to his abdomen, imagining Karen's hands touching him. He reached in his boxers and pulled himself out, gripping the base of his cock. He slid his hand up his shaft slowly, his thumb and forefinger pinching the tip as he passed it. He groaned, wishing it were Karen touching him this way. He wrapped his fingers around himself again and bucked his hips up into his hand, his breathing shallow. He heard Karen moaning in his head, saw her body shuddering, her eyes staring and-

"Jack."

Jack's eyes shot open and he gasped when he saw Karen standing at the end of his bed, her hands on her hips and a smirk on her mouth. He didn't try to scramble to cover up; she had caught him red handed. Her eyes were fixated on his hand which he realized was still pumping his cock and a surge of electricity seemed to shock his body. She was watching him get off like he watched her earlier. Then, in a flash, she was on the bed with him. She had her knees on either side of his thighs, her hands gripping the edge of her dress, the same dress from before, and she watched intently as he rubbed one out. 

"What are you thinking about?" she asked, her voice just above a whisper.

Jack gulped and shivered, staring her down as she watched him. He licked his lips and answered her honestly. "You."

She shifted, moving further up his body and planted her bare feet on the mattress on either side of his hips. She swatted his hand away without any protesting on his part and then she lowered herself down, his cock filling her up. She stayed their for a few beats and Jack let the sensation overwhelm his body, a shuddering breath falling past his lips. He raised his hands up to touch her, but she fixed him with a glare so he settled for gripping the sheets. She placed her hands on his chest to balance herself and lifted her hips up, squeezing the tip of his cock with her muscles. Jack cried out loudly, almost coming right then and there. He heard Karen laugh under her breath, but the sound was replaced with a moan as she lowered back down. He opened his eyes to watch himself disappear inside her with ever buck of her hips and he began to thrust in time with her, pushing up as she rammed down. 

Her nails dug into his chest and her breasts bounced, nipples hard and begging to be touched. He's not sure when she took off her dress, but he didn't give it a second thought as he felt himself nearing his orgasm. The sound of skin against skin, moans, gasps, and sighs clouded his brain and he squeezed his eyes shut as he came. The feeling seemed to last forever, the muscles in his legs straining and his deep breaths causing his throat to feel soar as air escaped him.

As the sensation finally dwindled down, Jack opened his eyes, utterly confused when he saw that he was alone. His softening cock was in his hand, his cum splattered over his thighs, hand, and the bed sheets and Karen was no where in sight. Realizing he imagined the whole thing, Jack stood from the bed on weak legs and walked to the bathroom to clean himself up. He was about to turn on the sink when another flash of Karen came forward to his mind. He reached for the shower faucet instead and turned it on freezing cold. As he stepped under the cold stream of water, he leaned his forehead against the cool tile and looked down at his cock, already jutting out again with Karen still at the forefront of his thoughts. He gripped himself back in hand and sighed.

It was going to be a long night.


End file.
